JEE Challenger
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Synthesis of Propane via Major Product Organic Reactions

Select the reaction(s) that yield propane as the primary product:

Options

A
Option A Diagram 1
Correct
B
Option B Diagram 1
C
Option C Diagram 1
Correct
D
Option D Diagram 1
Correct

Step-by-Step Solution

To determine which of the given reactions yield propane (CH3CH2CH3\text{CH}_3\text{CH}_2\text{CH}_3) as a major product, we analyze each reaction option step-by-step:

Option (A): Soda-Lime Decarboxylation

  • Reactant: Sodium salt of butanoic acid, CH3CH2CH2COONa\text{CH}_3\text{CH}_2\text{CH}_2\text{COONa} (Sodium butanoate).
  • Reagent: Soda-lime (NaOH+CaO\text{NaOH} + \text{CaO}) and heat (Δ\Delta).
  • Reaction: CH3CH2CH2COONa+NaOH→CaO,ΔCH3CH2CH3+Na2CO3\text{CH}_3\text{CH}_2\text{CH}_2\text{COONa} + \text{NaOH} \xrightarrow{\text{CaO}, \Delta} \text{CH}_3\text{CH}_2\text{CH}_3 + \text{Na}_2\text{CO}_3
  • Explanation: Heating the sodium salt of a carboxylic acid with soda-lime causes decarboxylation, removing the carboxylate group as sodium carbonate (Na2CO3\text{Na}_2\text{CO}_3). This produces an alkane containing one less carbon atom than the parent carboxylate salt. Starting with 4-carbon sodium butanoate yields 3-carbon propane as the major product.
  • Result: Produces propane.

Option (B): Kolbe's Electrolysis

  • Reactant: Aqueous solution of sodium butanoate, CH3CH2CH2COONa+H2O\text{CH}_3\text{CH}_2\text{CH}_2\text{COONa} + \text{H}_2\text{O}.
  • Reaction: 2CH3CH2CH2COO−→ElectrolysisCH3CH2CH2−CH2CH2CH3+2CO2+2e−2\text{CH}_3\text{CH}_2\text{CH}_2\text{COO}^- \xrightarrow{\text{Electrolysis}} \text{CH}_3\text{CH}_2\text{CH}_2-\text{CH}_2\text{CH}_2\text{CH}_3 + 2\text{CO}_2 + 2e^-
  • Explanation: Electrolysis of an aqueous solution of sodium carboxylate leads to decarboxylation at the anode to form alkyl free radicals (CH3CH2CH2∙\text{CH}_3\text{CH}_2\text{CH}_2^\bullet). Two such propyl radicals dimerize to yield a symmetrical alkane, nn-hexane (C6H14\text{C}_6\text{H}_{14}), as the major product.
  • Result: Does NOT produce propane.

Option (C): Reduction of Monohalide with Zinc and Acid

  • Reactant: 1-chloropropane (CH3CH2CH2Cl\text{CH}_3\text{CH}_2\text{CH}_2\text{Cl}).
  • Reagent: Zinc and dilute hydrochloric acid (Zn,dil. HCl\text{Zn}, \text{dil. HCl}).
  • Reaction: CH3CH2CH2Cl+Zn+H+→CH3CH2CH3+Zn2++Cl−\text{CH}_3\text{CH}_2\text{CH}_2\text{Cl} + \text{Zn} + \text{H}^+ \rightarrow \text{CH}_3\text{CH}_2\text{CH}_3 + \text{Zn}^{2+} + \text{Cl}^-
  • Explanation: Treatment of alkyl halides with zinc metal in an acidic medium leads to reduction of the carbon-halogen bond to form the corresponding alkane. Here, 1-chloropropane is reduced directly to propane.
  • Result: Produces propane.

Option (D): Reduction of Geminal Dihalide

  • Reactant: 2,2-dibromopropane (CH3CBr2CH3\text{CH}_3\text{CBr}_2\text{CH}_3).
  • Reagent: Zinc (Zn\text{Zn}).
  • Reaction: CH3CBr2CH3→Zn, reductionCH3CH2CH3\text{CH}_3\text{CBr}_2\text{CH}_3 \xrightarrow{\text{Zn, reduction}} \text{CH}_3\text{CH}_2\text{CH}_3
  • Explanation: Geminal dihalides (gem-dihalides) undergo complete reduction upon treatment with active metals like zinc to form the corresponding alkane, replacing both halogen atoms with hydrogen atoms to produce propane.
  • Result: Produces propane.

Conclusion:

The reactions in options A, C, and D produce propane as the major product.

Correct Options: A, C, D